Base- and metal-free visible-light driven site-selective α-C(sp³)–H functionalization reaction of glycine derivatives with hydroxamic acid derivatives

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(11), P. 3119 - 3123

Published: Jan. 1, 2024

A visible-light-mediated radical–radical cross-coupling reaction between hydroxamic acid and N -phenyl glycine derivatives under base metal free conditions is reported. series of unnatural amino acids peptides were obtained in good to excellent yields with chemo-selectivity.

Language: Английский

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Visible Light-Driven Flexible Synthesis of α-Alkylated Glycine Derivatives Catalyzed by Reusable Covalent Organic Frameworks

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1657 - 1668

Published: Jan. 19, 2024

Herein, we report a heterogeneous visible light-driven preparation of α-alkylated glycine derivatives. This approach employed β-ketoenamine-linked covalent organic framework (2D-COF-4) as the photocatalyst and N-hydroxy phthalimide (NHPI) esters alkyl radical sources. Numerous derivatives, including dipeptides, were precisely efficiently alkylated under reaction conditions. Based on excellent photoactivity compatibility 2D-COF-4, this alkylation could proceed flexibly in green solvent (ethanol) without any other additives. The fruitfully recycled with simple workup procedure, revealing high ecoscale value low environmental factor (E-factor).

Language: Английский

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Dual Photoredox and Copper-Catalyzed Asymmetric Remote C(sp³)–H Alkylation of Hydroxamic Acid Derivatives with Glycine Derivatives

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 14, 2025

Dual photoredox and copper-catalyzed remote asymmetric C(sp)3-H alkylation of hydroxamic acid derivatives with glycine via a 1,5-hydrogen transfer (1,5-HAT) process has been realized. The reaction was characterized by redox-neutral mild conditions, good yields, excellent enantioselectivity, broad substrate scope. This protocol provides straightforward efficient strategy to prepare highly valuable enantioenriched noncanonical α-amino acids. Moreover, the potential synthetic value this demonstrated in late-stage dipeptides high diastereomeric ratio.

Language: Английский

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Recent advances in electrochemical deoxygenative functionalization of alcohols and their derivatives

Tetrahedron Chem, Journal Year: 2025, Volume and Issue: unknown, P. 100126 - 100126

Published: March 1, 2025

Language: Английский

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Visible-Light-Driven α-C(sp3)–H Bond Functionalization of Glycine Derivatives

Catalysts, Journal Year: 2023, Volume and Issue: 13(12), P. 1502 - 1502

Published: Dec. 8, 2023

The glycine motif is widely prevalent in bioactive peptides. Thus, the direct and precise modification of derivatives has attracted significant attention over past few decades. Among various protocols for derivatives, visible-light-driven α-C(sp3)–H bond functionalization emerged as a powerful tool to achieve this objective, owing its merits atom economy, selectivity, reaction simplicity, sustainability. This review summarizes recent advancements derivatives. contents are organized based on photocatalysts employed modes process. mechanism, challenges encountered, future trends also discussed, enabling readers understand current developmental status field.

Language: Английский

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α-Benzylation of N-Aryl Amino Acids

Synfacts, Journal Year: 2023, Volume and Issue: 19(11), P. 1164 - 1164

Published: Oct. 14, 2023

Key words iridium catalysis - benzylation visible-light-promoted reaction

Language: Английский

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